Lisa – From Accounting to Real Estate Investing

Lisa – From Accounting to Real Estate Investing

#31 – Hailing from the Cayman Islands, Lisa Hylton has always had a career where she crunched numbers, although who she was crunching numbers for has changed dramatically over time. After doing part of her university degree in Cayman, and then transferring to the University of Georgia to complete it, Lisa began her career in accounting with Pricewaterhouse Cooper. After establishing herself at home, she then sought to take her talents abroad via a PwC exchange program. After considering New York and Toronto, Lisa eventually decided on Boston and packed up to move countries once again. 

It was in there, in Boston, where she really began to shine in her field, but with all this success came sacrifice. Vacations were sparse, so after years of hard work, Lisa finally took an extended tried to the west coast and upon returning, decided that a move was in order. She packed up and transferred to the PwC offices in Los Angeles and continued with the same work ethic she has exhibited in Boston. 

Years later, Lisa began to wonder what she would command if she tried looking for work outside of her company. This search led to her first major pivot as she became the controller of a real estate investing company. It was while working there that she began to understand the value of real estate and she started doing some research. Now, 2 years later, Lisa is on Career Crossroads to tell her story and make a big announcement about the future of her career path.

Lisa can be found at the following locations

Website: lisahylton.com

Instagram: @lisahyl

Podcast: The Level Up REI

You can find Career Crossroads at careercrossroadspodcast.com or follow us on social media

Instagram: @career_crossroads

LinkedIn: Career Crossroads Podcast

Twitter: @jcollaton

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The below transcript is A.I generated with light editing and may not be 100% accurate.

Transcript
Jonathan Collaton:

Good morning, good afternoon or good evening, you're listening to career crossroads. And if you're new here, welcome, otherwise, welcome back. I'm Jonathan Coulton, and this is the podcast where I talk to one person each week about all of the decisions that led them to their current career path. And then I try to figure out some lessons that the rest of us can learn from their journey. Today, I'm talking to Lisa Hilton, who is currently a real estate investor in Los Angeles, California. That, however, is a relatively recent development in her career. So let's listen to her story and find out how she got there. Lisa, welcome to career crossroads. How's it going today?

Lisa Hylton:

I'm good. How are you doing, Jonathan?

Jonathan Collaton:

Fantastic. As as i can tell from your video in mind looks like we're both in a bright sunny days today in our respective locations. Because you and I are in very different locations. I am Toronto based, but you are based around Los Angeles.

Lisa Hylton:

Los Angeles. Yes. And I'm super excited to be on your podcast,

Jonathan Collaton:

super excited to have you. You're another one of those great people who through the power of the internet, I've met online, and we actually met connecting in a podcast group where we were just kind of sharing ideas. And I had you share your career story with me. And I thought I got to have you on the show. This sounds like exactly what my audience needs to hear. So really excited that you're going to get to share everything today. Now, we always start off on career Crossroads by talking about what people were like in high school. Because I really think that that's where people really begin to make a lot of decisions about what they're going to do after high school. However, I always say to people, if there's any major moments in your life prior to high school that you need to mention that kind of influence what you were like in high school. Tell me about that as well. So tell me your story around the time you were in high school.

Lisa Hylton:

Yeah, totally. So I am originally from the Cayman Islands. So I was going to high school in the Cayman Islands. And you know, there was a lot of things going on in high school. I was a very active student in the sense that I liked to, like I was involved in sports and teams and stuff like that. So I played netball. And I remembered like all like scuba diving and all this kind of stuff sailing as a part of like high school physical education programs, and then just studying. But I would say that for me, you know, a good pivotal point was probably when I was around 15. Up until that point, I always thought that I wanted to be a doctor. And I was just really like, like, that's sort of what I was sort of aiming towards. And it was around that time I got an internship, I sought out an internship at the local hospital in the Cayman Islands. And they would allow students to come in for like four or five weeks to, to work in any of the different departments. So I asked to work in pediatrics. And they were like, yeah, this is really popular, but you can't spend your full five weeks hear, you can do like three weeks hear, but you have to pick another department to work for the remaining weeks. And I go Okay, great. What are the other options, and then they showed me all the different options. And I decided to choose accounting and finance as the second one just as as a whim. And I then went to do the internship pediatrics was first. And I noticed that every time the nurses would come to draw blood, I would always just feel really queasy and like not very good. And then they became like, Oh, you know what I realized that blood is just not, I just don't do well with blood. And then from there, you know, so that sort of rule things out for me in terms of the medicine area. And then right after that, I ended up going to the second department, which was accounting and finance. And I was like, Oh, you know what, I think I like this, this seems interesting. That's how I got my first like introduction to it. I wasn't sold that I did accounting and finance was what I was going to do. But it was the first introduction to like, Oh, you know, this is what it's all about. And then I went back to school. So I'll pause there.

Jonathan Collaton:

Sure. Yeah, that's a pretty dramatic shift. Right. And I guess I I was actually surprised when you said that was even kind of an option. Because I guess in my head like if you're going to intern at a hospital, you'd think it would be for purely medical purposes. But of course a hospital like any other business has human resources and finance and facilities staff and so they do need people in all these other roles. But I have to imagine how big of a mental shift that's got to be for you knowing that you have this goal of being a doctor. All of a sudden, one of the main things that you're going to have to contend with blood is, is a bit of an issue. And so you, you end up doing this internship there, that's for something not even medicine specific. It's finance, like finance would be anywhere else is just in a hospital. So that's got to be a pretty major shift to kind of mentally go through if you were really feeling like being a doctor. And my question from that is, was there any specific thing that led you towards wanting to be a doctor? Was it like something you saw on TV? Or a movie you saw? Or a family friend or something like that? Or what really was driving you towards that?

Lisa Hylton:

You know, that's a good question. When I think about it, you know, I don't think like, I can't say that my parents told me to be a doctor. But I do remember, like, just conversations when I was younger, as a child, that like, oh, like, these are some good careers, like are, these are some good jobs that you would want to go after? Like, yeah, you want to be a doctor, or you want to be a lawyer or something like that?

Jonathan Collaton:

An engineer? Yeah, a lot of it comes up a lot with people, I talked to you that parents are such a major influence early on in particular, right about the decisions that you make. And I think a lot of that has to do with the fact that everybody's life is sort of planned out to an extent up until the end of whatever the high school equivalent is of a country they're raised in. And after that, is when you really have to start making decisions. So at that point, parents are so sort of pivotal in, in what you know, because they are the ones who have influenced you the most. So you had this this finance, accounting experience. And I, you mentioned that you said you'll pause there. So I think Yeah, to continue, there's more headed in that direction. Tell me tell me where you went next.

Lisa Hylton:

So then I went back to school, I had one more year left. And in the cayman islands in the school that I was going to it was a British school. So you essentially have subjects. And one of my subjects was Business Studies, hence the finance and accounting, but then I also had sciences as well. So then went back to school and finished up. And I feel that that internship, and that experience sort of helped me to get like really focused because I came back to school and like, really studied to you know, sort of finish and finish up my my classes and be able to, you know, pass and get good subjects. But connected to that. Once again, in the Cayman Islands, they have like at that time, they had like a book of scholarships that you could go through and like apply to the different companies for scholarships to go to the college, go to school, both locally in the Cayman Islands, as well as abroad. And then that's where I was looking for scholarships to go to school for business, not necessarily accounting, but for business. And it just so happened that I was applying to all these different companies. And one of the companies that responded to me was PricewaterhouseCoopers. And they are an accounting firm. And they then ultimately, they ended up issuing me a scholarship. And they said, the terms of our scholarship of accepting this money is that you're going to study accounting. And I was like, Ah, okay, and I knew that going in. And I was like, open to the idea, because I was like, You know what, I think accounting would be good. And that's how I that's how my career and accounting began. I took that scholarship, went to the community college in the Cayman Islands, did two years and then transferred to the University of Georgia, and spent three years there finishing out my undergrad degree. And when I got to UGA, when I got to the University of Georgia, I realized that that school, you had to apply to the business school. And this was my next challenge, because initially, I didn't get accepted to the business school. And once that happened, I was like, Oh my god, this is like terrible, because like, I know that I'm getting this scholarship money to study accounting. So like, I can't like change my major to something else. So I ended up speaking to people and ended up in front of the dean and saying, pleading my case. And she said, okay, you know, you did well on the accounting portion of the exam, but your ICT portion that they gave wasn't like super strong. So what we're gonna do is we're going to allow you to come in and take just the first intermediate class of accounting. And then if you pass with a B, then you'll be in the program. And that's literally how I got in the program.

Jonathan Collaton:

Yeah, so you definitely have to do some advocating for yourself in order to get into that program. And now one thing I want to ask about there is it's always so curious to me, the wrap Now for anyone who is an international student, like you could go anywhere in the world, right? So I went to university an hour away from my hometown. And and now here I am all these years later back in Toronto, but for you like how, how Georgia? How did that happen? You could go anywhere, so what is the link

Lisa Hylton:

Yeah. that got you there? Ah, you know, two things. Number one, the firm PwC was they said they would only offer scholarship money if I went to an American school. So that was that. Secondly, I had applied to a couple American schools, but I had also applied to some British schools as well, because I was dating at the time someone, this guy, and he was in the UK, I met him in came in, but he ended up moving to the United Kingdom. And I was thinking I had gotten accepted to schools in the UK. But they got ruled out because I didn't have any funding to go to schools in the UK. And I was getting more funding to go to schools in the US. And then I had, I knew two other people who had actually went to the University of Georgia, one had just finished, I believe, and then another was actually like, a schoolmate of mine, and she was actually still there. And they both had really good things to say about their experience. So once I got accepted, and I spoke to them, and I was like, Okay, yeah, my parents were just, like, just go to this go to this school, don't bother about all these other schools. So yeah. So that's how that ended up happening.

Jonathan Collaton:

I always I always love to hear that kind of what the logic is, because there's, like relationships, particularly at that point in people's lives always play such a part. So it's really interesting to hear that that, if not, was the deciding factor, it was certainly part of the decision you had to make. So so you get into this business school after advocating for yourself. Right, right. And was that experience challenging? Because you at first, were not in the school? Like, did you feel like you had to kind of catch up in any way? Or was that really something that was already a skill set of yours, that you just had to sort of prove because of the scholarship situation?

Lisa Hylton:

You know, that is such a great question. Um, it has taken me several years to get to this point, in terms of like, you know, I am, I'm now like, 36. So like, I've been an accountant for many years at this point. And I understand accounting and the whole nine yards. But I don't feel like it was something that came easily to me. It was definitely challenging. And, yes, like, the cohort that I started with, like when you start, you typically start with three accounting courses, and then a couple others. So I only started with one, because I was on this probationary period. So yeah, so after that, I did catch up and pick up the rest of those classes. And it was challenging to go through the entire program. But I did it. And I got through it, and then ultimately got through the CPA exam, as well. And you know, came home and started my career. So but yes, it has definitely been a challenging road for sure.

Jonathan Collaton:

Yeah, and one thing we should probably point out right now, for anyone listening, keep sticking around for the rest of the interview. Because even though you're still an accountant, that's not where this whole story is going. So there is some major pivots coming I know. And so one thing I also want to know about the scholarship you got was that sort of dependent on you getting a an education, and then coming back to work for that company?

Lisa Hylton:

Yes, that's right

Jonathan Collaton:

Okay. Like at the end, you were coming home No matter what,

Lisa Hylton:

correct. So at the end, I was coming home, and I needed to maintain certain types of grades, in order to keep getting more money to pay for more for more schooling. So all of that happened. I definitely, you know, there were there were a lot of hoops. But I did get through all the different hoops. And then ultimately, I came home. And I worked in came in with the firm for four years. And once I started my first year, I found out that you could go abroad to live. And I was like, wow, with the firm. And I was like all my like, I'm totally interested in doing that. How does that happen? And that was a process more hoops, which I essentially jumped through everything that I needed to jump through in order to make it happen. And that happened in 2010 and 2010. If listeners remember that's like, the US was coming out of a deep recession. And there was a person ahead of me in 2009, who was actually trying to go to PwC Toronto, and Peter was he Toronto was like No, like, we're just not taking people from other like, we're just not how And people right now. So 2010 came and I was very hesitant, I just didn't think that it was going to happen. And I, you know, I was scared. And I decided that I was going to reach out, you know, on my own to try and make things happen, which ultimately backfired. But in the end, I ended up going to the right place, because I ended up moving to Boston in 2010, with the firm, and I spent four years there working. And those were definitely some very challenging years, I was on some very challenging projects. But I learned a lot from the experience. And then after four years of being...

Jonathan Collaton:

Let's not move on to beyond that yet, because you made some very interesting comments there that I want to dig into. Sure. You said that you reached out and it backfired on you. And so that was it. Was that to the Toronto officer or where?

Lisa Hylton:

Great question. So um, so this time, I was dating someone who was in New York, and I decided I wanted to move to New York. So I was in conversations with my firm in Cayman to move to New York, and they were not ready to, you know, begin the process. And I was like, well, maybe I'll just transfer instead of like going on a secondment. And I decided to reach out to the HR in New York on my own. And, ultimately, about a month or two later, my firm and came in was like, oh, we're ready to send you now. So we're gonna reach out to New York. And he has so then New York was like, hold on what's going on? Does this girl want to transfer does she want to go on? It's called second met? Do you know where one firm sort of sends you to another firm to work for a couple of years. So then that's where both of those things sort of clashed. And then ultimately, they were just like, you know, we don't want to do this. And I was just like, Ah, so the partner who was my partner in came in was like, You know what, I think you should go to Toronto, I actually have contacts in Toronto, and I was like, Okay, fine. You know, I I messed up. So I'm just gonna go with the flow. So Toronto it is. And they reached out to Toronto, and it was like March or April, and Toronto hadn't responded. And time went on, and the guy was seeing his sister was supposed to have a baby shower in Haiti. And it was the earthquake, it was the year that they Haiti had that massive earthquake. So they decided to push the baby shower to later on in the year in Boston, where she lived. So this was now August, and we had reached out to Toronto from like, March, April. And they had not responded. So August came, and I said to HR, listen, I cannot reach out to Boston, because I already messed up New York. So can you guys, I'm going to Boston for this baby shower. I would like to go to Boston. So can you find out whether Boston will have an interview. And that's how I ended up getting an interview with Toronto and Boston. All in like, the same time both offered. And then that's how I ended up going to Boston.

Jonathan Collaton:

Okay. Wow. So So first off, if we if we go back even a little bit before when you finished university, and you went back to Cayman, was there a guaranteed amount of time that you had to stay working for PwC? Or you would have to pay back part of that scholarship? Was that a thing?

Lisa Hylton:

Yeah, that was a thing too. I think I needed to have done like maybe a year or two? Not very long, but like a year or two? Yeah.

Jonathan Collaton:

Interesting. Now, that doesn't seem long at all, considering it's a multi year scholarship from the sounds of it. And I mean, if you don't want to get into the numbers, we don't have to but like, was it a sizable scholarship? Like, is it because my thought here is that the reason companies would offer this is they want people to have a certain area of expertise, but they needed you to go abroad somewhere to get that and then they want you to come back and do that for them. Right. So Sure. Is that Is that how it kind of knows?

Lisa Hylton:

So how it is really is and I don't know if Cayman still have this book of scholarships that they had back then, you know, because it's been a couple years now. But the point is, the M came in we are a small country. And one of the ways that the government encourages or yeah encourages companies that move there are two who make money there and hire, you know, people and etc. One of the ways they ask them to give back is in the form of scholarships, so helping local Caymanians to go to school so that way they're qualified and can have the opportunity to take some of these jobs that these companies are creating on the island, because otherwise that they do have to hire experts, you know, people from other countries Lots of Canadians will go to came in, I don't know if they still go now. But like back when this was like oh six, lots of Canadians, a lot of British, a lot of South Africans, Indians, they would come in to came in to work. And typically they'll come and they'll come in at a certain level in the organization. And they'll typically work for two to three years. And then some will stay. And then they continue to grow in their career and become partners. And then others will decide that they want to pivot and move on to doing something else. Either they'll stay in Cayman or they'll go home, or they'll go to a different jurisdiction altogether. So that is, like, it's not like they are just sort of, like, Yes, they're doing it out of the goodness of their heart, too. But like, they're it's a it's a joint effort between the government and companies to provide that additional education and support to Caymanians. And it's been, it's been awesome. I'm truly grateful for that experience. So yeah,

Jonathan Collaton:

Fantastic. So when you decided then to leave, and this whole like Boston, New York, Toronto thing that's kind of chaotic.

Lisa Hylton:

Yeah.

Jonathan Collaton:

I can't believe it took four months for you to have to sort of wait to hear back from from the Toronto office. But I guess the dough show like the state the economy was in at that point in time too.

Lisa Hylton:

Yes, the economy was...exactly.

Jonathan Collaton:

Yeah. I mean, I was in university back then. And my mother was laid off from her job for a while I got laid off from my summer job one year. And so, you know, we were solidly middle class. So I know how much other people struggled during that time, because just jobs were tough to come by. And so it makes sense in that regard that like, they weren't exactly looking elsewhere to find people to employ, because there weren't people around Toronto that that need to work as well. Eventually, you did get that interview and you get the Boston interview. And I guess, you know, you mentioned the, the family member of your partner at the time had a sister or cousin

Lisa Hylton:

Yeah, sister, yeah,

Jonathan Collaton:

sister, and she was gonna have the party in Haiti, but instead it's in Boston. Like, is that the sole reason why you just said like, Boston, that's where I'm going to apply or was there? What did she live there?

Lisa Hylton:

she lived there. And because, you know, back in March, April, when the earthquake took place, like, you know, I didn't, I wasn't Boston wasn't really on my radar. It was like number two, because it was close to New York. So number in my choices, like number one was like Boston, and then number two, and then Toronto. So yeah, so that's how it was that yet that's sort of how it came into play. I think it was, maybe it was number three. I can't even remember now. It's been so long.

Jonathan Collaton:

Yeah, no, I get it.

Lisa Hylton:

But it was around that it was it was in my top three.

Jonathan Collaton:

Yeah. And like, no offense to anyone in Boston. It's a top three city, right. It's totally your second choice. And you're devastated to only be in Boston, Boston's amazing. I've been there myself.

Lisa Hylton:

Yeah.

Jonathan Collaton:

Love it as a city.

Lisa Hylton:

Awesome city.

Jonathan Collaton:

So cool. All this old history there. So what's what's that like to transition from moving from Cayman to Boston? And you've already had the experience of doing that international move for university. But still, I have to imagine it's a different experience when you're now you know, when you when you're in university, there's a bunch of people all around you all your age, and they're all doing the same thing. You're all there to learn and have a certain experience. But the working world is a different beast. There's people in a 40 plus year age range, all working together. And everybody's at a different stage of their life. They've got different priorities. So what's that like to move to Boston and start working there?

Lisa Hylton:

Yeah, totally. It was challenging, but it was also very, it was also it was also a really good experience, but it was definitely challenging. So like, one, whether like, that's the first thing like come on. Like came in is like, warms 80 degrees, and then you go to Boston and Boston has all four seasons. So yeah, it was like I definitely by the third year of living in Boston, I knew how to dress the whole nine yards, but in the beginning, I would arrive somewhere like in like sweat because you just don't know how to like properly, you know, balance how much to wear in the commode. So, so whether for sure. Culturally, so Boston is like an Irish pub type town, you know, going on sports. So culturally was a little bit it was a little bit challenging, but eventually I did find I like to dance. Specifically salsa and now moving to LA I dance tango, but we'll get to that. But um, back then I danced a lot of salsa and one day I found I googled and I, the first two years, all I did was pretty much work. Just work a lot and some time in my By the end of the two years, and then at the beginning of my third year, I'd gotten promoted. And I also was like, you know, what, if my time ended in the city, I would not have seen the city at all. And I think it's time to like sort of balance, seeing the city and then also continuing to build my career. And that's when I discovered a salsa place in, in the Boston area, I would take the train everywhere, and it was in Cambridge, and I would go there, and I would dance salsa, and it was just so amazing. And I really loved it. And then I was also really into yoga. So I would go to like a yoga studio near my house. So honestly, what Boston taught me was, it taught me to, like, really think about the things that I really like to do, and then find community around those things. So if I'd like salsa to go find salsa communities, if I like yoga, the same thing. And then eventually, I also met friends, randomly one day, I was on a train, and I met a girl. And I always say that she was like the domino effect. Because after I met her, I met tons of people. And my, it totally changed my entire Boston experience from a social point of view of like, meeting friends and, and meeting people. So

Jonathan Collaton:

yeah, and it seems like given what you just said, there, it sounds like you're very, very career driven. And because you know, all these moves you were looking at before seem in a lot of ways based off the job and yeah, and less about the social. Like you weren't afraid to go somewhere where you you didn't know somebody, it just happened to be that you knew some people in Boston, but right, but even still, you were very driven for those two years. It sounds like and career focus, then you got the promotion? And was that sort of a leveling out of sorts, where you felt like now that I've achieved this, I can relax a little bit and enjoy things a little more, or am I off on that?

Lisa Hylton:

Um, you know,

Jonathan Collaton:

I mean, I don't know if it doesn't sound like you totally take your foot off the gas or anything like that. But you can say like, if my if my career here ended tomorrow, I wouldn't have seen anything.

Lisa Hylton:

Yes, yes. Yes. Yeah, it did. If it definitely once the two years, once I got to that two year point, made that promotion, and came to that realization. Yeah, definitely. And then, you know, shortly thereafter, I actually took my first break from my job. So this was, once I got into my third year, the firm HR said to me, you know, what are your plans? And I said, What do you mean? And she goes, Well, do you want to stay in Boston? Do you want to leave? Do you want to make partner here? Do you want to do something else? What do you want to do? And I said, You know, I hadn't really thought that far ahead. Like, I had only thought up to this two year bit. And so she was like, Well, you know, give it some thought, you know, we're trying to figure out our headcount. And we want to, like be able to provide you with the best kind of experience and stuff. And she was like, you know, couple questions you can ask yourself is, where does your allegiance lie? Does it lie in the city that you live in, or in the industry that you work in? Because if it's the industry, then you could be flexible to going to a different city, that could enable you to continue to grow in your industry, which was financial, which has been financial services. Or if you are, if your allegiance lies to living in Boston, then, you know, maybe you want to consider being flexible on your industry. So maybe you want to, you're okay with pivoting into because big for like, they have a lot of different industries. So you could go, yeah, so you could just pivot into another industry and still keep growing in your career. So I took some time, it took me a little while, I want to say maybe three to six months to really think about that. And that's when I decided that I wanted to do number one, I was thinking about moving to San Francisco, primarily because I had never been there before. But I had just heard about it. And I sounded similar to Boston, and I was like, Oh, you know, maybe that would be a good fit. So in April, many years ago, now I can't probably 2014 because that's the year I moved to brought to LA. So 2014 April, I took a trip to San Francisco. And I remember getting on the flight thinking it was gonna be three hours and then realizing it's six. But yeah, getting out there. And I was like, oh, wow, this is awesome. So I actually found a yoga program, a yoga teacher program at this studio out there call yoga tree for one month, and I would do I would do this yoga teacher training and like live in San Francisco to to get a feel for the city to determine And whether I'd want to move there,

Jonathan Collaton:

yeah, what's the one month the amount of time that you were going to take off? Or was it more than that?

Lisa Hylton:

Just it was gonna be that? Yes. Okay.

Jonathan Collaton:

Um, two things I want to get into about that. One is the line that you said about, I guess it was HR saying, like, where's your allegiance? At first I thought that was going in a bad direction. I'm like, Oh, no, this is like, a slave to the company type of mentality. But no, the the idea of, of like, that quote is exactly why I do this podcast so people can understand that there are different reasons for everyone. Right? Some people are committed to the city and some are committed to the job or the the industry industry, that's a better term for for sure. And so like, that's an amazing line. So thank you for saying that. Because I really think people will resonate with that when they hear that. And the second thing that I find interesting when you said you were you decide to take some time off. I really think that's so fascinating to see the difference in everybody's mindset of like, what constitutes time off work versus a long vacation? And because I would think of a month as like a long vacation, but you sit, you know, when we were talking about those two years, we just like worked. And yeah. Did you take a lot of vacations or was this No. So this for you was, and you're nodding along? That's why I'm saying no, people can't see this. But yeah, so yeah, vacations weren't a big part of your life. So this one month was like a really big lifestyle shift for you.

Lisa Hylton:

Yes, it was.

Jonathan Collaton:

Okay, nice. Yeah, tell me all about it, then.

Lisa Hylton:

And luckily, you know, I worked in the Big Four. And the big four offers these kinds of sabbaticals where you know, you don't lose, you don't go to zero in your salary. So you just get a little bit of money for the month that you're off in, in that particular situation. But as the story goes on, it gets interesting. But, but yeah, you know, so I did that. And the firm didn't have any room in San Francisco. And I ended up my mom had came out with her husband, and we decided to drive down to LA, and I came down to LA. This was in the summer of 2014. This was around July 4 weekend. And I was like, you know, LA, this is not my kind of city. And my mom is like, Oh, I love hair. I love it. Yeah, if you move, move hair, and I was like, No, this is not the place. And I remember calling one of my partners in Boston and telling him, you know, the situation and he said, Well call this partner in LA. They have needs in LA, and I called him and he said, Yeah, and we chatted, and he was like, How soon can you start? I said, Oh, September 1, September 1, I'll come and he goes, perfect. So I went back to Boston, early July, right after July 4 weekend, went to see each HR and HR was like, yeah, you know, what's, what did you decide? And I said, I'm going to move to LA. And she goes perfect. We because we need people in LA. We're going to help you move.

Jonathan Collaton:

Oh, yeah.

Lisa Hylton:

And I said, Wow,

Jonathan Collaton:

that's amazing. Like that is, that is the best sort of, I want to call it luck. But I also don't think it's luck. Because you and I were talking before we started recording and I said to you like I'm kind of a believer in like, if you...and I've said this actually on the podcast before when I've interviewed people, like tell other people what you want, because if they can help make that a reality, mMost people are good people, and they try and do that. So that's awesome. That that worked out for you.

Lisa Hylton:

Yes.

Jonathan Collaton:

And I was actually gonna ask about the logistical side of this, like, did you? Did you just have an apartment that you could give up easily in Boston? Did you have to deal with selling property or any of that?

Lisa Hylton:

No, thankfully, no. So I was on my lease, my landlord, I just told him the situation. And he was like, Yeah, no problem. Because you know, Boston's market real estate market had changed drastically since 2010. In the sense that when by time I left in 2014, prices for apartments now were much higher.

Jonathan Collaton:

Your landlord was happy to have you leave.

Lisa Hylton:

Of course.

Jonathan Collaton:

Raisie the rent.

Lisa Hylton:

He was like Yeah, no problem. You can go We'll raise this rent and get it up to market.

Jonathan Collaton:

I'll bring a dolly, let's get you out of there.

Lisa Hylton:

So So yeah, so the firm helped me to move across the country. It was just a really smooth move, couldn't you know, no complaints and I moved to LA. And I remembered moving out here on the plane and I was just in tears because I was so like, scared. Because this city was so big. It was the biggest city I'd lived in to date came in tiny Boston tiny, and you know, it's bigger than Cayman, but it's still smaller than LA for sure. And then, you know, desiring to go live in San Francisco which was going to be inside of my comfort zone because it's quite close to Boston, and then ending up in LA, which is like totally outside of my comfort zone completely. But six months in, you know, I was like, wow, this is one of the best decisions that I made. But it took those six months for me to sort of get climatized and like to find my bearings and to find my feet, to then to sort of say, Okay, yeah, yeah, this is what is gonna happen.

Jonathan Collaton:

I'm so glad that you said that you were scared on the flight over there. Because I it up to this point, I've just, you know, not knowing you, you just sound like the super confident woman who just like I'll move to New York or Toronto, Boston, whatever, I'll go to university in another country, whatever, I got this. But the reality of career changes for a lot of people are that there is there's a vulnerability in that there is like scary new experiences you have to deal with. So I'm really glad that you're kind of willing to share that because I, I think there are just some people who won't, you know, they Yeah, I talk about it, like, you know, you go look at Instagram, and everybody's showing this amazing, perfect version of their life. But nobody talks about how like, It was terrifying for them to get to this point, or, you know, not every day is amazing. And so I really, really glad that you're able to share that. So then tell me more about the LA experience in that job. Were you doing the same type of stuff in the role?

Lisa Hylton:

Yes. I feel that, you know, as my story continues, I just going through this story with you, I can, I sort of can see the ramp up to like where I'm at now. Because like, choosing to move from Boston to LA, I know that one of the things that I could rest my anchor in is that I knew who my employer was. So as I flew on that flight to LA, to land in the city to create life, and to build a brand new community, I left Boston with a couple things. One, I knew my employer, so at least I knew who I was dealing with in terms of job, and I knew the consistency and all of that stuff. And then secondly, Boston, going back to what I said earlier, I recognized by the year three, that, you know, what were the things that I really loved. And I found those communities. So once I came to LA, that's what I did, I went looking for salsa, and then from salsa, that's how I got introduced to tango, and then found an amazing Tango community of people and, you know, continuing to grow in my career. With the firm, I spent another two years with them. At the 10 year mark, I decided to make the decision to leave, which looking back to me at that point in time felt like one of the hardest decisions to make, because I had been with this company now since college. And I was just like, oh my god, like I just can't envision leaving. However, what prompted that was I came out here and I was working on this client that we had been auditing for almost 20 years. And they decided that they wanted to give all of the audit work that we had been doing this massive team of tons of people to another competitor, Big Four. And overnight, we went from pretty much having the client to not having the client. And that then brought me back to the same question that HR asked me a few years earlier when I was in Boston, which is where does your allegiance lie? Does it lie in the city that you live in? Or the industry that you work in? And once again, my now my answer was different. So after two years of living in LA, I decided that I was willing to change my industry to continue to live here.

Jonathan Collaton:

Ohh, I like that. Perfect. That is, and that just goes to show to how, like you don't have full control over your career. Right your employer is...they need to make money. And if they can't make money, you didn't exactly say that, like people were going to get laid off. But I suspect there weren't. It didn't feel like everybody was going to be around there a few months later whether it was critical chose to move on their own...

Lisa Hylton:

People were moving

Jonathan Collaton:

People were moving. Yes.

Lisa Hylton:

And the firm is helping them. So this is where it so that question really came in handy. And I remember sharing with other people, hey, you need to think about this. So that way you can then tell the firm, hey, I'm willing to, I'm willing to move or I want to stay in this industry. So if you're willing to stay in the industry, so that means you might end up in another city and to be open to that or maybe it's that you want to take another job. So their response was I ended up moving into banking. I had also experienced another promotion. That promotion came with a Paid sabbatical or paid four weeks off. And I decided that, wow, this is perfect, why not take? I have a history of not taking vacations. So I had a lot of time. So I asked them, Hey, could I take, I think it was two months off. So I asked if I could take two months off. And they looked at the calendar, and they were like, yeah, you know what, why not? It's the summertime, you can take it. And I ended up going to Italy, and I traveled in Italy for two months, a month and a half, because I came back to LA and spent two weeks in LA before restarting work, dancing tango doing all kinds of tourist stuff. And, and I was paid this whole time because of the four weeks of from the from the promotion, and then vacation time that I had not used.

Jonathan Collaton:

That's awesome.

Lisa Hylton:

Yeah, it was crazy.

Jonathan Collaton:

So cool. And like I'm sure we could, we could have a whole long convo, just about the intricacies of how different companies deal with vacation time. And that's probably I think, you know, instead of getting into the whole convo, it's probably just worth saying, for people who are thinking about whatever job they want to look at, like really consider how your employer manages paid time off or unpaid time off vacation, all those things, because if you have an employer that's willing to allow those longer, sort of times where whether it's it's paid or unpaid, like that's not everybody has that ability. So

Lisa Hylton:

Right.

Jonathan Collaton:

And not because people aren't interested, but because the employers can't sort of manage that level of staff movement or staff time off. So exactly, certainly something for people to consider while they're looking at various employers.

Lisa Hylton:

Yeah, for sure. That's one of the perks of I think working in the Big Four is like they have the seasons. Right. So then once you're out of certain when you're no longer in that busy season period, you could negotiate for some of this kind of stuff.

Jonathan Collaton:

Yeah. And just to clarify, because I think I know who they are. But the big four are PwC, Deloitte, KPMG.

Lisa Hylton:

Yes. And EY - Earst and Young

Jonathan Collaton:

Ohhh EY Yeah. Yeah, I don't know. Maybe they're not as big in Canada, because I'm not as familiar with them. Whereas I know the buildings for all the other three in Toronto. so

Lisa Hylton:

sure, sure sure.

Jonathan Collaton:

Anyway, so tell me then, when you got back and you spent this time off, did that change your outlook in any way? Like, did you feel like...now, and I'm a traveler, so yeah, this is kind of me projecting onto you. But for me, like I can imagine, after working so hard to then have this ability to take that much time off.

Lisa Hylton:

Yeah.

Jonathan Collaton:

And having sort of done that before. All I wanted to do when I got back is do more of that. Is that how you felt? Or did you just feel like recharged and ready to get back to work in this new industry?

Lisa Hylton:

Well, I felt recharged, you know, like I didn't, at that point in time, I didn't sort of see it as a lifestyle is something that I could do, like a long term. So you know, I came back and I was like, Okay, let's get started. And I stayed maybe at the firm for another month to two months. And that's when I decided, you know, what, let me just check what the market would give me if I was to leave, and I did. And that's how I ended up leaving after 10 years to take another job, you know, so an investment manager.

Jonathan Collaton:

So you were only in that banking specific area role for like a month?

Lisa Hylton:

Yes.

Jonathan Collaton:

Wow. Yeah, that's, that's, on the one hand, I hadn't thought about all this time, these 10 years working there that, because you're not in the market, there's that sort of Tango with the company, like, here's what they can offer you. And here's what you're willing to accept as compensation. And if you're happy with it, great. But at the same time, the market might be offering something totally different.

Lisa Hylton:

Yes

Jonathan Collaton:

And if you really weren't even looking, how would you even know? So a month in, was it...was it anything about the job that you were doing that you just, you didn't find the jump as interesting?

Lisa Hylton:

So it's funny that you asked that because I being in LA, my request was entertainment, media and technology, like that's the industry I wanted to transfer into. And then they were like, Ah, well, we can't really like it's just it, you know, just wasn't working out. And it was like, Okay, this is a since you want to stay in LA. You know, biking is sort of the industry that we do need someone in and I said, Okay, so yeah, so I just sort of said, Okay, this is not really my first choice, but I'm going to, you know, let me just look and see what the market will will offer. And then once I looked, I saw the market would you know, I got this opportunity to work for an investment manager in working on real estate. Private Equity real estate funds as a contract. And I said, You know what? I'll do it. Let's go. So after 10 years, I decided to quit to leave and take the job. And I knew someone who was working there. But I want to say, a month after I got hired, she gave notice and laughed. And I was like, oh, my goodness, like, what did I do? Like, what kind of places this like if she's, she just laughed. And but I, yeah, I stuck in there. And I learned a lot from that experience. I remember her telling me, you know, it takes six months for you to figure out what you're doing. And then another six months to determine whether you like it or not.

Jonathan Collaton:

You have people giving you great advice this whole time.

Lisa Hylton:

Oh, yeah.

Jonathan Collaton:

Oh wow. You're so lucky. All these people amazing advice for you. So, okay, after, it seems like you said, it was an amazing experience. So six months, and you figure out what you're doing six months later, you decide you like it?

Lisa Hylton:

Yeah, I decided that I liked it. And what it did for me at least it unveiled to me what real estate could do. So I grew up in a real estate family. My father was a contractor, and he built 14 apartment units. So as a child, I grew up like cleaning and helping with apartments and stuff like that. And, you know, my parents sort of were all about, make sure you go to school, get a job. They were not like, oh, make sure you invest and like build more apartments and like stuff like that, that there wasn't really the conversation they sort of had with us. So when I was in Cayman, I did buy my first place when I was working at PwC. And was a two bedroom two and a half bath townhouse. But I bought it because I loved it. I didn't buy it, because oh, I ran the numbers. And they make sense. But I quickly realized that I needed to have considered that. Because once I did buy it, and I tried to rent it, a broke even the first year and then it lost money every single year for five years.

Jonathan Collaton:

Oh, so you kept it when you went to the States.

Lisa Hylton:

Yes, I kept it in Boston, and I was an out of country landlord. And then I moved to LA and I still had it. And I remembered being in LA, because here is where I made the decision to sell it. I want to say about a year after I moved here, I got a bill in my email for like $1,000. And this was not a property, this was a property I was floating. So I was putting money into it in order to have it. And then now I get $1,000 bill from the AC company because the AC broke down and the tenant called the AC company. And I said oh my goodness, this has got to go, I have to sell it. So at that point, I had to hold on to it for about five years. And I you know, called the broker, the Yeah, the real estate agent. And I said, Hey, can you help me in selling this? She said, Yeah, no problem. It took about six months, almost almost a year, but it sold. And after that sold, I was still working at PwC at the time. And I remember saying, I am totally sworn off of real estate, not happening not going back there. And then life has a sense of humor, because I ended up taking this job working for private equity real estate funds. And, you know, six months in, I started to figure out what it what it is that I was doing. And then six months later, I was like, Oh, this is how this is. So then I started listening to podcasts is like bigger pockets and like going to meetups on real estate and like sort of getting educated to learn about like really understand and learn about real estate from a perspective of an investor. And all this time I'm like still working and like and then I started thinking, oh, maybe I could buy a place here in LA and like house hack. But then the properties were like 700 and 800 thousand dollars for like a house and I was like, Ah, this is not gonna work. And then I wanted like a duplex because I like to have my own space. So I wanted to do like say a duplex and the duplexes were like a million dollars and I was like, Okay, this is not working out. So I went from that to then turnkey, looking at turnkey and other cities, Alabama, Detroit, but all the time I kept remembering my first experience. So I always sort of wanted to make sure that I wasn't buying a property like I really understood the expenses. And like really understood the rental income to make sure that this was something that was cash flowing and that I would not need to be floating it.

Jonathan Collaton:

And it seems like, when you're talking about first you're looking at these places in LA right where you live in work, but then when you're looking at Detroit and Alabama and these other places was that then purely a, I will rent this out and just make money off this.

Lisa Hylton:

Correct.

Jonathan Collaton:

So you were looking at multiple options here where either you live in a duplex, or you would rent out a house somewhere else.

Lisa Hylton:

Yeah, well, it was, it was an evolution. Like I didn't, I didn't come out the gate wanting to do out estate. I first started with, okay, I wanted to, you know, just invest locally, like, see what I could do hair. But then I quickly realized based on my desires, like what the kind of lifestyle I want to live and my choices, that it just sort of didn't really work for me. So that's how I then ended up looking out of state.

Jonathan Collaton:

Okay. All right. And so what's the timeline then, like year? or How long were you working at this point? Because I think we've jumped around a little bit. So yeah, at the time, you're looking at real estate investing? Are you already working at the real estate? Or investments company?

Lisa Hylton:

So I started working at the investment company, in 2016. And I want to say that I started really looking at Real Estate seriously, probably sometime in 2017. After like, maybe working there for about a year, I was like, wow, like, there's something here like, I just need to figure out like, how to do this properly. Because obviously I wasn't doing it properly the first time.

Jonathan Collaton:

It doesn't seem like investing was really on the brain the first

Lisa Hylton:

right no it wasn't.

Jonathan Collaton:

You're like I want to live here. This is a nice place.

Lisa Hylton:

This is nice. It's pretty.

Jonathan Collaton:

now when you first started thinking about investing, though, was that just as an option of like, this is just a way to bring in more money, like a just a good way to invest?

Lisa Hylton:

Yes. 100%

Jonathan Collaton:

And it was just passive on the side thing, and you had your main job, Right. Totally that's 100% how it started. Okay, and, but I feel like there's been an evolution in that, given what I think you're doing now. So, tell me then how you end up from from that, as you know, on the side, I just want to bring in some rental income to what you're doing now.

Lisa Hylton:

Sure, sure. So I remembered a friend of mine that I met, I have a good friend of mine that I met when I was living in Boston. She said to me, You know, when she met me, she was like, you know, have you considered doing this program called landmark? And I said, No, and I've never even heard of it. And she goes, you know, I'd recommend checking it out. And she'd always say to me, like, maybe yearly. And then finally, when I was in LA, and I was going through a little bit of a challenging time, she said to me, you know, you should check out this program. And I said, Okay, so I went online, and I found that, oh, the program was like two buildings down from where I worked. And I said, Wow, okay, I'm in LA. If it's something like that happens to you. It's like it's it's a layout. Because this city is like travel travel-zilla.

Jonathan Collaton:

Yeah, we have bad traffic in Toronto, and we have the biggest highway North America on the north side of Toronto. However, it's not great in Toronto, but I hear like nightmares far worse than I've ever experienced when it comes to traffic around LA.

Lisa Hylton:

Yeah, LA traffic is no joke. So if you can, like literally walk to this place, which was my situation, I said, Okay, I gotta go check it out. So I went checked it out. Definitely an amazing program. Through going to that program, I met a lady and got introduced to syndications. So this was real estate, investing passively into commercial real estate. So everything from apartments to retail to hotels, the whole nine yards, and I said, Wow, like, when I got introduced to the like, when I met her, she didn't just off the bat share this with me. We were in this program for about six months. And then towards the end, one of the other girls said, Hey, like we should exchange business cards we did. And then once we exchanged business cards, I saw that she was a real estate investor. And I was like, Oh, I'm into real estate investing. And she goes, Oh, really? And then, you know, I said, like, I definitely want to call you to learn more, through her bat through her card into my bag, never called her three months later, I was taking a little staycation a week off. And I found her card in my bag was cleaning out my bag, found her card and I said whoa, I was supposed to call this lady. So I called her and then learned about her business. And I said, Wow, like I had no idea that this was even possible. I just thought like you had to be like some kind of big investment manager like the one I work for in order to do this and in order or you need to be some institutional investor that had met gazillion dollars. to like, invest in these things, and I just got exposed to a whole other world. And yeah, from that experience, I, you know, I started that exposure then led me to other things because she had somewhat of like a mastermind. And through that I got exposure to podcasting, video blogs, the whole nine yards. And I realized that there was aspects of myself that I was probably good at a lot of other things that I hadn't ever really been exposed to that I didn't actually expose myself too. Because it just never crossed my mind.

Jonathan Collaton:

There's a great saying that, like, we don't know what we don't know.

Lisa Hylton:

Yeah!

Jonathan Collaton:

And I think that really applies there that until you actually have the chance to sort of like rub shoulders with someone who's doing something other than them what you know about, right, I'm gonna imagine that at PwC. And wherever you're working after that, like, you're really just working with people who did the same thing you do a lot of the time. And so you don't have that kind of exposure. And I know as like you said, You're 36 I'm 31. And so much of my friend circle is people I work with people that know the job that I'm doing. So like, there isn't always that level of diversity in terms of learning, totally outside experiences. Because

Lisa Hylton:

Totally, when you're an adult, that's how you meet people is to work often and and you've got to have these other sort of runnings. And, and I want to just highlight really quick the value of business cards, because I think, you know, you might give out 100 business cards, and maybe 99 of them get thrown out. But it costs you like $10 to make those cards and someone three months later finds one in a backpack. And I've been in that same situation as you where you find a card, somebody gave you months prior and all of a sudden it can have this like massive impact like that 20 cent little card can have a huge impact on your life. Right. So

Jonathan Collaton:

yeah, just crazy how that happenes.

Lisa Hylton:

Yeah, totally crazy. So yeah, that's how I, you know, started with that part, I made my first investment. And during this time, I'm still working, you know, I'm still building my career, not really looking to be like, Oh, I'm trying to start a business or anything of that nature, like, is just purely just investing in real estate, in addition to continuing to work. And then as I continued to water, these other talents and skills, and as I continued to network and meet more people, in the fall of 2019, I decided that I wanted to start a podcast. So I embarked on this, you know, you know, to start and everything. And, you know, from doing all of that I realized, wow, like, I feel like there's a lot of different sides of me that that I'm just not utilizing. And I want to say the other side of the coin too, is once I took this job, this job, unlike my job before, doesn't accrue vacation time.

Jonathan Collaton:

Hmm.

Lisa Hylton:

So because of my nature of just being someone who will work a lot, I didn't really take a lot of vacation. And I also was just more because I was also very invested minded. Like I ended up I just made different decisions. So some of the decisions I made was like, I want to say three years ago, I moved into Inglewood, which is a part of Los Angeles that is still up and coming but has more affordable rents. So while I'm still making, you know, really good money, and I could go live in the Marina, I just chose to you know, be able to save my money and move into hair. And then on top of that, cut down on travel, and then spent more money in terms of education. So like, really this getting into masterminds getting into getting around other people that were doing things that were very different from what I've been exposed to. So it really just changed my mindset. And it opened up my mindset completely. So yeah, as I continued to do that, I then began to think you know, what, why couldn't I not build a business a syndication business myself, and once I got to that place, it was like, Whoa, like, you know, I was met with a lot of internally, it was met with a lot of like, doubt and uncertainty. And I sat with that I want to say for maybe about a year and a half of of like thinking about it continuing to build my podcast, but like also thinking about building and then through that same woman that I met, I had an opportunity to do like a sub syndication with a few other ladies, which is creating a little syndication of our own to then invest

Jonathan Collaton:

I think I'm gonna get you to need to define syndication. for me to make sure I understand this fully. So tell me what that really means.

Lisa Hylton:

So syndication is where you essentially provide opportunities for people to invest in projects that are fairly large that they would not have been able to invest on their own. So they are essentially syndicators will pool funds to invest in like a real estate deal, or it can be even a business or something else all together. So that's sort of what syndication pretty much is. Okay, great. So with that, I continued to work, my job continued to, you know, show up, do all the different things that I needed to do. And then after about almost a year and a half of sort of doing that reaching the two year mark of continuing to build the business, as well as so podcasts building out website, thinking about email campaigning, thinking about attracting investors, talking to investors, while also still working full time, you know, 12 hour days, and then COVID head and then having that all come in house. And like sort of continuing to build it through COVID. I decided in towards the end of March to focus on building my business. March 2021

Jonathan Collaton:

Yeah, just happened.

Lisa Hylton:

Just happened, yeah.

Jonathan Collaton:

Okay, so major changes coming your life, right now.

Lisa Hylton:

And it's been. For me, I think, one of the things that kept coming up for me was that I felt like I was constantly in this tug of war with trying to work as fast as I can for my employer. And then to get all of the deliverables that they need to get done to them. And then also then trying to do the things I need to do in order to build and push my business forward. And then getting to a place where you're just tired. You're just totally burnt out, like, because you're just burning on both ends of the candle. And I kept saving through this entire time. And I kept looking and thinking, running the numbers in terms of my expenses to say, Okay, I know how much it takes me to live in California. If I didn't change living, Do I have enough money? And then Do I have enough money to also cover business expenses, in terms of like running my podcast, and like everything else? So once I did the numbers and got to that place where I could see okay, yeah, you know, I'm at a good place, I've covered a lot of the basics in terms of creating the website and all this stuff for my business. I said, Wow, like, I think, I think I'm almost there. And like, before leaving, I want to say, like, I knew I was gonna leave eventually, I just didn't know when. And I've remembered in 20, in 2019. So this is long before the decision to even leave. This is something a bit personal, but I was at a place in my dating space where I was just not meeting anyone. And like anyone that was on the same trajectory in terms of sharing the same values and wanting the same things out of life. And I decided at that time that I was going to explore the process of freezing my eggs, primarily because I heard that the company would provide support financial support to do it. So in 2019, I went to go check it out. And when I checked it out, I chickened out, because I got scared. And I was just like, you know what, I'll just wait, maybe it's not going to be necessary. And then 2020 came and 2020 has been crazy.

Jonathan Collaton:

Yeah, dating certainly a little harder.

Lisa Hylton:

Yeah. It's, it's been challenging you like, you know, you can still meet people by feel like people are at a different place in their life, you know, for a variety of different reasons. Yeah. So I decided towards the end of the year, after dating tons of different people in 2020. I said, Okay, I need to sort this out. I'm just going to shut down all the dating and just get this sorted out. So I actually signed up, I reached out to the doctor in in December and I was like, hey, I want to do this. They booked me appointment to put come in and everything and essentially, I went in and what was supposed to start in January ended up starting in December and ended up getting finished in January as opposed to finished in February. And once I finished that I felt a very large load being left out like taken off of my back because I know that, you know, once, what as a female, once you get to this point in your life age wise, like this, just, there's just certain realities of life that just comes with the territory. So that helps me a lot. And then yeah, and then, once I got that sorted, I then started taking a look at my business, I knew that I was going to sign up for another coaching program. I had been eyeing these people for about a little over a year. And I'd been following them. And I really, really like them a lot. And I decided to take the plunge. And I remember the first call I had with theirs. It's a two person, there's two women. And the first call I had with her, I was telling her the situation of balancing everything. And she said, Have you considered giving yourself a chance, giving yourself 12 months to just focus on building your business and go all out? And he said, I'm so scared. Because I've never not had a paycheck. And I've never not had a job. And she was like, Well think about it. I you know, I thought about it. And I had been thinking about it. So yeah, you know, I did, I went did all the different things like, you know, get my eyes checked, get the dentist done. And then once everything was done. And then once I got to the place where was like, okay, everything is set, this was like March ish, I then had to make the call to my boss to say, hey, um, I want to resign. And that was one of the hardest calls to make. But I felt like I was mourning the loss of, of my identity of like who I am. And you said earlier, you know, about being driven and career focused. And to get to this point in my career, after spending almost 15 years, driving this career forward to then say, Oh, you know, what, I'm gonna start at Ground Zero to build a business that I think has the ability to impact people in ways that I know is, like, I know, it has the ability to impact people in massive ways. But to give myself the chance to, to fully focus on it. And that's how I ended up here.

Jonathan Collaton:

Wow. And so a lot of powerful stuff going on in that that's be so for one that like, that's very personal story. Thank you for sharing that because I do I, I understand the realities that like everybody faces of, we can't just separate your career from the rest of your life. They're so intertwined, right? Like you were working, as you said, like 12 hours a day, that's literally half your day, on some days. Your career is sometimes it is your life at points, right. And, and on top of that, working on the side to do all this other stuff to get your business now up off the ground. I also I want to provide, I think, an alternate perspective, because you said, you feel like you were or you felt maybe maybe you don't now, but you certainly felt like you were leaving this this identity behind. But I don't think you are because what I'm hearing is you had to use all of the skills you've built up over the years in your career to actually get this business up off the ground like you. You mentioned running the numbers and think back to what you said a very beginning Well, yes, you probably through where you bought the house in Cayman, and you did not at all run the numbers and it ended up being a financial loser for you. But you've taken everything you've learned in 15 years of financial management accounting and and now you've applied that to this new real estate investment business. And, and so you are the same person, you've just evolved. You've taken that that identity and added a new dynamic to it. I think that's an outsider's perspective.

Lisa Hylton:

I appreciate that. I appreciate that. But yeah, you know, it's it's still raw, like my last day will be April 15th. And we're recording this hair on April 4.

Jonathan Collaton:

Yeah, and I think this episode is going out on April 14th.

Lisa Hylton:

Oh, wow. But when you said you know, you also said something earlier about you know, like being brave, you know, like, this has been a there's been a lot of tears. There's been a lot of tears, but you know, just really believing in yourself. And I think the other thing for me is, recognizing I'm coming full circle, in the sense of the unknown has brought a lot of uncertainty has brought me a lot of anxiety in the past. And now it does. But being willing to sit with that unknown, and to reassure myself that it's gonna be okay, and we're going to play full out, and we're gonna give it all that we've got. And I have like a mantra that I have one of my mantras, which is, I could try and I could fail. Or I could try and be wildly successful. So we're in those moments when I have doubts. And when things get scary, I come back to that place. Whether I'll stay in LA or not, is to be seen. I'm not attached to it. I love living here. But I will reassess as the months unfold, or as the weeks unfold. But yeah, it's a very, it's a very, it's a time that has lots of emotions, you know, there's definitely fair, and I remembered before I made the decision, I was telling my girlfriend that I could feel the arms affair holding me. Because, like, I knew what the next step was to be. But up until this point, like I had never, like made such a decision. And thinking back at moving from Boston to LA, I had that anchor. You know, I knew that my employer was good. But like making this decision, especially at this time, in the market, when a lot of people don't have jobs, and we are tech, we are in a recession. But this is a time when businesses are born. This is the time it takes people who are willing to take that risk, and they could fail. But they could also be they could change the lives of for themselves and other people. So with that is what I I just keep coming back to myself and saying, I'm just gonna keep showing up and doing the best that I can.

Jonathan Collaton:

So yeah, amazing. Oh, that is so good. Now I, I know that brings us to where you are now and right. But I can't let you go without telling me or telling the listeners, where can they find your podcast? Where can they find your company if this is something that they're interested in?

Lisa Hylton:

Yeah, totally. So I help people, I help busy professionals invest in real estate without being a landlord. And I do that because I know what it's like to work, many, many hours, make really good money. And I have been counseled in the past to buy a home and to do all these different things. But I encourage people to think about using their money to generate streams of income. So investing it in assets that actually generate cash flow. And that's the opportunity that my business seeks to provide to people who are interested in this kind of stuff. And yes, I do have a podcast, it's called the level up Rei. And my podcast is focused on having conversations with real estate investors. I do have conversations with passive investors every Thursday, the first Thursday of each month. So that enables my listeners to get a feel for other people who are investing passively and their experiences and how they've dealt with the ups and downs of passively investing in all different types of real estate. And then I just bring on the show a variety of different people. So everything from operators who are operating and all the different asset classes to come on to share their experiences, their journey, their story to get to know them, and then you can find me at Lisa hylton.com and that's Hilton with a Y so just like the Hilton Hotel only thing with a Y.

Jonathan Collaton:

That's it. Awesome. And I will put links to all those things in the show notes. So if you just go to my website, you can find the links to all of those there. Lisa, thank you so much. This is a roller coaster journey soda. It's crazy because the big like, it was like a long crank upward and then the crazy windy journey right near the end. And I'm hoping to see how successful because I know we'll be successful, I want to see how successful it is for you down the line. So thank you so much for sharing that today.

Lisa Hylton:

I appreciate it. Thank you for having me.

Jonathan Collaton:

All right, so that is Lisa's career path so far. Accounting and Cayman and now real estate investing in LA. So let's talk about what we can learn from her journey. Although real estate investing for the sake of investing is relatively new in terms of her career. This is not her first experience with real estate. Back when she was living in Cayman, she had bought a place just for the sake of having a really nice place to live. And then when she left came in, she kept it and he proceeded to lose money for five straight years. And the straw that finally broke the camel's back was a $1,000 bill for a broken air conditioner. And that was it. She was done. And she sold her place and swore off real estate. But years later, she gets a job as a controller for a private equity firm. And suddenly Her eyes are open to the power of real estate and how it could change her life for the better. And I think it's important to realize that while the job is the catalyst for her to think a different way, Lisa was humble enough to accept that she didn't know much about real estate investing at that time. So she starts doing her research. She listens to podcasts, she goes to meetups to learn from the perspective of an investor she takes courses. And then once she had enough information, she started small. She continued to learn as she went and spent two years building up her own syndication before she was ready to make it into a full time career. And she had a lot of setbacks along the way that caused her to modify her plans. House hacking wasn't going to work, duplexes in LA were too expensive. All of a sudden, she's looking at turnkey in Alabama or Detroit. She went through this whole evolution in her 30s to find out that she actually did have an interest in something that she had had a bad experience with earlier in life. So the lesson that I think we can take from that is that you shouldn't just abandon an idea for the rest of your life because things didn't work out the first time. I think of it in the same way that our taste changes over time. And five years ago, maybe you didn't like a certain food. But if you try it again, now, maybe you will. So when it comes to something that you suddenly have an interest in in terms of your career that you thought in the past was never going to be in your future. start slow. dip your toe in the water, see how it feels. And if the waters the right temperature, slowly work your way in. That's what Lisa did. And now she has an entirely new career because of it. I also think that Lisa has shown us that investing not only in property, but in yourself can pay off. It just takes time. Lisa told us she spent two years building up her business. But she also said that in that time, she committed resources to training and opportunities to get around more business people to help her network and grow her knowledge of the industry. And then in the fall of 2019, she decided she wanted to start a podcast. And well, we didn't talk about it, I would guarantee that the conversation she's had on her podcast have contributed significantly to what she's learned about investing since she started. So I hear that and it's clear that Lisa had a plan. She had a plan to obtain the skills, the contacts, and to get the branding presence required to ensure that she could one day have a successful business. And she had to put in a lot of hours on top of her regular job to get to that point. And she was probably making no money at first. But now on April 15 2021. One day after this episode is released, she will be totally independent and working for herself. And the lesson from that is to be patient. Rome wasn't built in a day, and neither was Lisa's business. So make a plan and stick to it. And eventually you will see results. I want to add to that though, that patience does not have to be boring. I don't know about you aut Lisa sounds pretty fired up when she's talking about real estate investing, when she's talking about how it has the power to change people's lives. I mean, I'm getting fired up just thinking about her enthusiasm for the career that she's built for herself. And I wonder if this is what my wife feels like when I talk about podcasting, although I doubt it. Anyways, it's probably time to calm down and wrap this thing up. So those are a couple of the things that I think we can learn from Lisa. But I am sure there are more lessons that you pulled out of this interview. And if you did, let me know about Through the contact page on career Crossroads podcast.com. I'd love to hear what others are getting out of these interviews. If you know someone who'd be interested in Lisa's career path, please share this episode with them. And if you want to hear more interviews like this, go to career Crossroads podcast calm, or find the podcast on Apple podcast, Spotify or any other podcast player out there. If you like what you hear, please leave the show a five star review on Apple podcasts or pod chaser. Or you can even leave a review directly on my website. While you're there, I hope you will subscribe to my newsletter which goes out every Wednesday and includes things like recent career articles I'd recommend and of course the link to the newest episode of the podcast. Episodes like next week's interview was Zack, who studied politics then became a paramedic in Canada, but now was in Belgium working on European healthcare policy.